How Short Challenges Can Spark More Joy Than Big Plans
Reflections from my eight-week “mini bucket list” experiment.
This post is a little different from my normal technology & business posts. If you’re here just for the tech stuff, feel free to skip this one, but if you’re struggling to figure out what gets you excited, what the next chapter of your life looks like, like doing experiments or are just curious about how I navigated a minor midlife crisis keep reading…
A few months ago, I reached the point in my life where I found myself seriously wondering what the next chapter should look like.
My 40th birthday was fast approaching. And as I reflected on my life so far, I realised I’d achieved pretty much everything I’d set out to do. House, family, friends, career, goals, hopes and dreams. Tick, tick, tick.
For the first time in my life I had absolutely no idea what I wanted to do next.
And so, like any overachiever who needs a project, I decided to spend the next few weeks figuring out what that next chapter could look like.
Weekly Reflections: A Simple Ritual
The plan was simple. Every Sunday morning I’d spend an hour or two doing a deep reflection on what happened that week. I wanted better visibility into the things I was doing each week, to see how my thoughts and wants changed.
At the same time I wanted to get out of my comfort zone and try new things. Maybe that would spark some ideas that would bring me joy and help me figure out what to do next I thought.
Treating each week like an experiment
I took the approach of treating everything like an experiment that I could reflect and learn from. This gave me confidence I needed to try new things. If they worked, great, if they didn’t then chances are I’d at least learn from it and have something to write about.
Thinking about it like an experiment made it so much easier to say yes instead of no when opportunities came up. And it’s helped me become a bit more of a risk taker and try new things more often.
The Mini Bucket List
Around week three, I had the idea of creating a mini bucket list. At this stage it was exactly two months until my birthday. And I was feeling particularly inspired to make the most of my time, but I wanted more than just the standard list of monthly goals.
I wanted to try and push myself to see how many new things I could do in a small period of time to fast-track my learning and get really clear on what I wanted.
The first version of the list was called 40 before 40. I was feeling quite creatively drained and struggling to figure out what I’d want to do, so I used ChatGPT to help give me some ideas. And yes, in case you were wondering, get another tattoo was absolutely on the list. Even ChatGPT knows you can’t have a midlife crisis bucket list without that one.
When I reviewed it with fresh eyes the next day I realised there was absolutely no way in the world I was going to do all those things, nor did I really want to.
My first thought was to scrap the idea completely, just go back to my normal approach of setting monthly goals. But at the same time, I really wanted to try something new, to see if there was a better way of approaching things that I wanted to do. To see if I could push myself to do more, but also not to feel overwhelmed. To feel inspired by the list rather than see it as a laundry list of things that had to be done.
The Framework
And so I refactored the list. Breaking it down into three sub categories, and reducing the number of items to around 20. The goal wasn’t to do everything. But to push myself, just a little, and to inspire me to try new things that I hadn’t done before.
Group 1 → Core goals (that will feel amazing if I get them done)
Group 2 → Progress counts (considered a win even if I don’t fully get them done)
Group 3 → Stretch goals / bonus list (ambitious, but also optional)
At the time a lot of the things on this list still felt unachievable, especially in a small period of time. So I removed the numbering, changed it to use bullet points and tried to really think of it more as a bucket list - things I’d like to do, rather than a fixed list of goals.
The simple act of removing the numbers and grouping into the categories helped the list feel so much more fun and achievable.
Momentum, Surprises and a Living List
Within two weeks I managed to tick off half of the tasks in group one, and quite a few in the other groups which took me completely by surprise. That had never happened so quickly when I set a list of monthly goals. That momentum carried me forward every single day and I found myself looking at the list thinking what could I tackle next.
I also found myself adding new things to the list. Having it as a living document with space to add new things worked really well for me. It allowed me to pivot as needed, without feeling like I needed a whole new plan or that I had to remove something to make way for something else.
The Power of Not Doing
That said, one of the biggest learnings from this experiment was from the things I didn’t do.
For the first six weeks there were 2 tasks at the top of my core goals list, that I just didn’t feel like doing. At first it felt a bit disheartening. I’ve made so much progress on this list, I can’t stop now, I just need to make time and prioritise them I’d say to myself.
But then one day I stopped and asked myself if they really mattered. Where they really the things that would make me feel amazing? No. They were only on the list because they were things I felt like I should do, because I’d previously told myself I would. And now they no longer felt like the top priority tasks that they did at the start.
Sometimes deciding not to do something matters more than the things you finish.
One was finishing a book I’d been reading - which, honestly, doesn’t matter if I finish now or ever. I have a tendency to start books and never finish them. Sometimes you can get what you need from the first few chapters, or sometimes the book just isn’t the right fit, right now. And I’m ok with that. There’s no point finishing a book just for the sake of it.
The other was making progress on a novel I started years ago. Both had been on my list because I felt I “should” do them, but they weren’t bringing me joy right now. Letting them go made space for projects that truly energised me.
The hangover of Big Challenges
One other realisation I had with this experiment was that I really like short challenges. I’ve noticed that sometimes when I have a big goal, or a big project that I’m working on, once I achieve it, after that initial high of woohoo I did it how amazing, I am left with what I’d describe as a kind of depressed hangover, which usually lasts for days. Instead of feeling happy that I achieved something, I feel depressed that it’s over, and like I desperately need something new to start to feel good again.
But shorter challenges, especially the ones where it doesn’t feel like a sprint or a marathon, they are my favourite, and they don’t give me the hangover. It gives me just enough urgency to focus, enough variety to keep me excited and enough closure to feel good without burning out or crashing after.
Four weeks is too short, but eight weeks feels too long. Six weeks feels like the sweet spot for me with challenges like this.
TL;DR / Summary of my learnings
Be flexible with your goals. It’s more than ok, if you don’t do everything. Progress beats perfection every time. And sometimes not doing something is actually better than doing it.
Consistent weekly journalling helps in more ways than I expected. It’s an easy thing to skip or not realise how much of a benefit it has, but I found whenever I missed a session, or even worse, missed two in a row thats where I started to spiral.
It’s ok if you lose momentum. Figure out what helps get it back again. For me it’s yoga + journalling and then creating something - usually a creative project, that sparks the momentum again for me.
Grouping goals into the three categories really helped and is something I’ll continue to do. It helped create different expectations for different types of tasks, and the variety also really helped keep me motivated.
Six weeks is my sweet spot. Long enough to make huge progress on the things that are important to you, while still being short enough that you don’t lose focus.
I am blown away by the progress I’ve made during this experiment. I’ve done a lot of things I didn’t think possible, and it’s been really interesting to see how doing those things just kept opening up doors and new opportunities.
One of the tasks I tackled early on in the project was defining my personal values and setting myself a 5 year plan. At the time it felt a little like a fantasy, but now I can see that it’s absolutely 100% possible.
Get another tattoo is still on the list. I didn’t get it yet, but it’s something I think about nearly every day…
I’m curious if others do experiments or projects like this? Do you set yourself mini bucket lists or short challenges? What works best for you? I’m planning my next one now. Any tips?
Well said! Thanks for sharing.